Process for preparation of 2-hydroxyalkyl imidazolidinones



United States Patent 3,248,399 PROCESS FOR PREPARATION OF Z-HYDROXY ALKYL IMIDAZOLIDINONES Wilhelm E. Walles, Midland, and Stanley S. Left, Bay

City, Mich., assignors to The Dow Chemical Company,

Midland, Mich., a corporation of Delaware No Drawing. Filed Apr. 25, 1963, Ser. No. 275,487

Claims. (Cl. 260-3091) This invention relates to processes for making 2-hydroxyalkyl imidazolidinones and to new compounds which can be thus made.

The reaction involved in the new process can be represented as follows:

wherein each R is hydrogen or an alkyl radical, at least one being alkyl. The preferred materials are those oxazolidinones having not more than one alkyl radical in either the 4-position or the 5-position, -i.e., at least one R in each of these positions is hydrogen. The most preferred materials are the S-alkyl oxazolidinones, especially those wherein the alkyl radical contains up to about 8 carbon atoms.

As is evident from the above formulas, the substituents on the Z-hydroxyalkyl side-chain of the imidazolidinone are the same as those on the oxazolidinone used as starting material, those in the 4-position of the latter appearing in the 1-position on the side-chain of the former While those in the 5-position of the latter appear in the 2-posit-ion on the side chain of the former. Carbon dioxide is a byproduct of the reaction.

The preferred oxazolidinones for use in the process of the invention are the 5-alkyl oxazolidinones, such as 5 methyl, S-ethyl, S-n-propyl, S-isopropyl, S-n-butyl, 5-sec.- butyl, S-tert-butyl, 5-hexyl and 5-octyl oxazolidinones. Another desirable type is the 4,5-dialkyl oxazolidinones, such as 4,5-dimethyl, 4,5-diethyl, 4,5-dibutyl, 4-methyl-5- ethyl, 4-et-hyl-5-propyl, 4-butyl-5-methyl and 4-hexyl-5- ethyl oxazolidinones. Also useful in practicing the invention are those oxazolidinones having 3 or 4 alkyl radicals in the 4 and 5 positions. The alkyl oxazolidinones may have inert substituen-ts on one or more of the alkyl radicals without affecting the course of the reaction, and it is to be understood that the use of such substituted alkyl oxazolidinones to make the corresponding alkyl im-idazolidinones is included in the present invention.

The process of the invention consists essentially of heating the oxazolidinone under an inert atmosphere at a temperature of about 2 25 -400 C. for a time suflicient to convert at least a useful proportion of the material to the corresponding imidazolidinone. The time required is inversely related to the temperature. Thus, at 310 C. about 3 hours are required to convert 10% of S-methyloxazolidinone while at 325 C. about 90-95% is converted within 5 hours.

The yield of imidazolidinone is improved if during the reaction period the'volatile and gaseous byproducts, particularly CO are continuously removed. This can be conveniently accomplished by operating under reduced pressure or by continuously purging the reactor with an inert gas, such as N The reaction may be conducted batchwise or continuously, though a continuous reactor would necessarily require a high capacity in order to provide the requisite long residence time.

The practice of the invention is illustrated by the following examples.

Example 1 Oalcd Found Molecular Weight.-. 158 160 Percent C 53. 14 52. 08 Percent l'-I 8. 9. 20 Percent N 17. 71 18. 50

The structure was confirmed by infrared analysis.

Example 2 When the experiment of Example 1 was repeated except that a slow stream of nitrogen was passed continu ously into the reactor during the reaction period, the yield of the imidazolidinone was 43% of the theoretical.

The novel hydroxyalkyl imidazolidinones of the invention are useful as chemical intermediates, particularly in the production of polymers and resins useful in finishing paper and textiles. Thus, they readily condense with formaldehyde to produce polymers useful for imparting crease-resistance to fabrics. Another use is in making esters useful as plasticizers for polyvinyl chloride and other synthetic resins.

We claim:

1. The process of making an imidazolidinone having theformula comprising heating under an inert atmosphere at about 225-400 C. an oxazolid'inone having the formula 1 1 t? Rg-C C:

wherein, in each of the above formulas, R R R and R are radicals of 1-8 carbon atoms independently selected from the group of radicals consisting of H and alkyl radicals, at least one of them being alkyl.

2. The process of claim 1 wherein at least 2 of R R R and R are H.

3. The process of claim 1 wherein R R and R are H and R is an alkyl radical of 1 to 8 carbon atoms.

4. The process of making N-(Z-hydroxypropyl)-5-meth- 3 yl imidazolidinone comprising heating under an inert atmosphere 5-methyl oxazolidinone at about 225-400" C.

5. The process of claim 4 wherein the temperature is 310-325" C. and the heating is continued for 1-5 hours.

References Cited by the Examiner UNITED STATES PATENTS 2,812,333 11/1957 Steele 260309.7 2,887,485 5/1959 Yost 260309.7 10 2,989,537 6/1961 Druey et a1 260--309.7

1 4 FOREIGN PATENTS 483,160 5/1952 Canada. 697,839 9/1953 Great Britain.

OTHER REFERENCES Gabriel et aL: Beriohte, v01. 30, pages 2494-97 (1897).

IRVING MARCUS, Primary Examiner. 

1. THE PROCESS OF MAKING AN IMIDAZOLIDINONE HAVING THE FORMULA 